Synthesis of 4,6‐Difluoro‐Tryptophan as a Probe for Protein 19F NMR

Abstract

AbstractA scalable procedure for the synthesis of 4,6‐difluorotryptophan is reported based on a deaminative coupling of a 4,6‐difluorogramine with 2‐benzylthio‐1,5‐dihydro‐4H‐imidazolone as glycine equivalent. Thus prepared 4,6‐difluorotryptophan was incorporated into the C‐terminal domain of the HIV‐1 capsid protein (CA‐CTD), and 19F spectra of the 4,6‐difluoro Trp CA CTD were recorded and compared to the singly fluorinated counterparts.